Novel isoflavone glucosides in groundnut (Apios americana medik) and their antiandrogenic activities

Marina Ichige, Erina Fukuda, Saki Miida, Jun Ichiro Hattan, Norihiko Misawa, Shun Saito, Takahiro Fujimaki, Masaya Imoto, Kazutoshi Shindo

研究成果: Article査読

26 被引用数 (Scopus)

抄録

Isoflavone glucosides (2′-hydroxy,5-methoxy genistein-7-O-glucoside (1), 2′-hydroxy genistein-7-O-gentibioside (2), 5-methoxy genistein-7-O-glucoside (3), 3′,5-dimethoxy genistein-7-O-glucoside (4), 2′-hydroxy genistein-7-O-glucoside (5), genistein-7-O-gentibioside (6), 2′-hydroxy,5-methoxy genistein-4′,7-O-diglucoside (7), and 2′-hydroxy genistein-4′,7-O-diglucoside (8)) were isolated from the groundnut of Apios americana Medik. Their structures were elucidated on the basis of HR-ESI-MS and 1D- and 2D-NMR analyses. Compounds 1, 2, 4, and 7 are new compounds presented here for the first time. Compounds 2 and 5 were proven to be androgen receptor antagonists due to their binding activities for androgen receptors (IC50 280 and 160 μM, respectively) and the inhibitory activity of androgen-induced expression of prostate-specific antigen (PSA) mRNA in LNCaP (prostate adenocarcinoma) cells (IC50 20 and 18 μM, respectively).

本文言語English
ページ(範囲)2183-2187
ページ数5
ジャーナルJournal of agricultural and food chemistry
61
9
DOI
出版ステータスPublished - 2013 3 6

ASJC Scopus subject areas

  • 化学 (全般)
  • 農業および生物科学(全般)

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